Quinoline nematicidal method

Abstract

A method of inhibiting a nematode population which comprises applying to the locus of a nematode, a nematode inactivating amount of a compound of the formula (1):

Het--X--CH₂ --CH₂ --Ar (1)

or an N-oxide or salt thereof, wherein

Het is a nitrogen containing heterocycle, for example 8-fluoroquinazolin-4-yl, or quinoline-4-amine,

X is O, NH, or CH₂ ; and

Ar is a substituted phenyl group, for example 4-(2,2,2-trifluoroethoxy)phenyl.

Description

FIELD OF THE INVENTION

This invention provides a new nematicidal method. There is an acute need for new nematicides and new nematicidal methods, because available nematicides typically have high mammalian toxicity and must be used at high rates. A nematicide that can be applied at lower rates and that has lower mammalian toxicity would represent a significant advance.

SUMMARY OF THE INVENTION

More specifically, this invention provides a method of inhibiting a nematode population which comprises applying to the locus of a nematode, a nematode inactivating amount of a compound of the formula (1):

Het--X--CH₂ --CH₂ --Ar (1)

or an N-oxide or salt thereof, wherein

Het is a group selected from: ##STR1## X is O, NH, or CH₂ ; Ar is a substituted phenyl group of formula (18), (19), or (20) ##STR2## wherein Y is O or S;

R¹ is (C₂ -C₅) alkyl, (C₃ -C₇) branched alkyl, halo (C₁ -C₄) alkyl, phenyl, or phenyl substituted with CF₃, CN or halo;

R² is H, F, or Cl, or R² combines with Y--R¹ to form --CH₂ --CH₂ --O-- or --O--CF₂ --O--; and

Z is halo.

DETAILED DESCRIPTION OF THE INVENTION

Throughout this document, all temperatures are given in degrees Celcius, and all percentages are weight percentages unless otherwise stated.

The term "halo" refers to a F, Cl, Br, or I atom.

The term "haloalkyl" refers to straight chain and branched chain groups.

The term "HPLC" refers to a high pressure liquid chromatography.

The term "inhibiting a nematode" refers to a decrease in the numbers of living nematodes.

The term "nematode-inactivating amount" is used to describe the amount, which is sufficient to cause a measurable reduction in the treated nematode population.

The term "peanut root knot nematode assay" refers to the test method described in detail hereinafter.

PREFERED EMBODIMENTS

While the compounds of formula (1) as a class are exceptionally active as nematicides, use of certain subclasses of these compounds is preferred for reasons of greater efficacy. More specifically, use of the following subclasses of compounds is preferred:

a) compounds of formula (1) that provide at least 80% control when tested in the peanut root knot nematode assay at 12 ppm;

b) compounds of formula (1) wherein Het is a quinoline group of formula (2);

c) compounds of formula (1) wherein Het is an 8-fluoroquinoline group of formula (3);

d) compounds of formula (1) wherein Het is a quinazoline group of formula (4);

e) compounds of formula (1) wherein Het is an 8-fluoroquinazoline group of formula (5);

f) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is halo(C₁ -C₄)alkyl;

g) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is selected from CF₃, CHF₂, CF₂ CF₃, CH₂ CF₃, CF₂ CHF₂, CH(CH₃)CF₃, CH₂ CF₂ CF₂ H, and CH₂ CF₂ CF₃ ;

h) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is a (C₃ -C₆) branched alkyl group;

i) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is a phenyl group that is substituted with one or more halo or CF₃ groups;

j) compounds of formula (1) wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is (C₂ -C₅) alkyl.

Use of the following compounds is particularly preferred due to their extraordinary activity Each was found to give 100% control when tested at a concentration of about 1 ppm in the soil against the peanut root knot nematode.

8-fluoro-4-[2-[4-(difluoromethoxy)phenyl]ethoxy]-quinazoline;

8-fluoro-4-[2-[4-(pentafluoroethoxy)phenyl]ethoxy]-quinoline;

4-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]quinazoline;

8-fluoro-4-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]-quinazoline;

8-fluoro-4-[2-[4-[4-(trifluromethyl)phenoxy]phenyl]ethoxy]-quinazoline;

8-fluoro-4-[2-(4-n-pentoxyphenyl)ethoxy]quinazoline;

8-fluoro-N-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]-quazoline-4-amine;

8-fluoro-4-[2-[4-(trifluoromethoxy)phenyl]ethoxy]quinazoline;

4-[2-[4-(4-fluorophenoxy)phenyl]ethoxy]quinazoline;

8-fluoro-4-[2-[4-(t-butoxy)phenyl]ethoxy]quinoline;

N-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]quinazolin-4-amine;

5-methyl-N-[2-[4-(trifluoromethyl)phenyl]ethyl]quinazolin-4-amine;

N-[2-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]ethyl]-quazolin-4-amine;

8-fluoro-4-[2-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]quinoline;

6-chloro-N-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]quinazolin-4-amine;

4-[2-[4-[4-(trifluromethyl)phenoxy]phenyl]ethoxy]pyrido-[2,3-d]pyrimidine.

Other preferred compounds include 4-[2-[4-(4- and 8-fluoro-4-[2-[4-chlorophenoxy)phenyl]ethoxy]quinazoline. (4-chlorophenoxy)phenyl]ethoxy]quinazoline.

The following table identifies specific compounds of formula (1) wherein Ar is a group of formula (18) or (20) and gives the results of testing them against the peanut root knot nematode, Meloidogyne arenaria, in the peanut root knot nematode assay. The peanut root knot nematode assay is carried out as follows. Each test compound is initially formulated as a 400 ppm solution by combining 19.2 mL of 0.05% solution of Tween 20 (polyoxyethylene (20) sorbitan monolaurate) in water with a solution of 8 mg of the compound in 0.8 mL of acetone/EtOH (9/1). The 400 ppm solution is then diluted with water to give a 200 ppm solution Three to four cucumber seeds are placed in 16 g of clean white sand, and 1 mL of the 200 ppm solution of test compound is added. This provides a concentration of the compound in the soil of 12 ppm. The cups are allowed to dry one to two hours, and then one mL of a concentrated (50 to 60 per mL) nematode (Meloidogyne arenaria) suspension is added to each cup. The cups are incubated for four to seven days. Then 11 mL of deionized water is added to each cup and the cup is gently shaken to rinse the nematodes from the sand. The suspension is poured into a watchglass and observed under a dissecting microscope at 15×-20×. An activity rating is given based on nematode mortality. Aldicarb, carbofuran, and fenamiphos are used as chemical standard compounds. Results are reported in the last column of the following table.

__________________________________________________________________________
Nematode
Results
Example                     MP   at 12 ppm
No.  Het
X  Y R1      R2
°C.
% control
__________________________________________________________________________
1    2  O  O 1,1,2,2-tetrafluoroethyl
H 70-72
0
2    2  O  O 2,2,2-trifluoroethyl
H 65-66
100
100
3    2  O  O ethyl        H 65-66
100
100
100
87.5
4    2  O  O t-butyl      H oil  100
5    2  O  O 1,1-dimethylpropyl
H oil  100
90
6    2  O  O 1-ethyl-1-methylpropyl
H oil  100
7    3  O  O 4-chlorophenyl
H 130  100
8    2  NH O ethyl        H 125-126
0
9    3  O  O 1,1,2,2-tetrafluoroethyl
H 70-72
100
99.5
70
10   3  O  O difluoromethyl
H 114  100
0
90
11   3  O  O pentafluoroethyl
H 92.5 100
100
12   3  O  O 2,2,2-trifluoroethyl
H 119  100
100
13   3  O  O trifluoromethyl
H 87-89
100
14   3  O  O 2,2,3,3-tetra-
H 75
fluoropropyl
15   3  O  O 2,2,2-trifluoroethyl
F 47-49
100
16   3  O  O 1-methylethyl
H 111-113
0
17   3  O  O n-butyl      H 80-82
100
18   3  O  O t-butyl      H 97-98
100
100
100
19   3  O  O 1,1-dimethylpropyl
H oil  100
100
20   3  O  O 1-ethyl-1-methylpropyl
H oil  100
50
21   3  O  O --CH2 --CH2 --
98.5 100
100
22   3  O  O n-pentyl     H 245  100
23   3  O  O phenyl       H 107  0
24   3  O  O 4-(trifluromethyl)phenyl
H 85.9 0
25   3  O  O 2,4-difluorophenyl
H 107  100
100
26   3  O  O 2,4-dichlorophenyl
H oil
27   3  O  O 3-(trifluromethyl)phenyl
H oil  0
28   3  O  O 2,2,3,3-tetrafluoro-
F oil
propyl
29   3  O  O 2,2,2-trifluoroethyl
Cl
oil
30   3  NH O 1,1,2,2-tetrafluoroethyl
H 168-170
100
31   3  NH O trifluoromethyl
H 198-200
100
100
32   3  NH O 2,2,2-trifluoroethyl
H 182  60
33   3  NH O 2,2,2-trifluoroethyl
F 193  100
100
34   3  NH O 2,2,3,3-tetrafluoro-
H 135
propyl
35   3  NH O 2,2,2-trifluoro-1-
H 163-165
methylethyl
36   3  NH O 2,2,2-trifluoroethyl
Cl
196
37   3  NH O ethyl        H 179-181
0
38   3  NH O i-propyl     H 124-126
0
39   3  NH O phenyl       H 109-111
60
40   3  NH O 2,4-difluorophenyl
H 168  100
100
41   3  NH O 2-fluorophenyl
H 192  100
60
42   3  NH O 2,4-dichlorophenyl
H 115
43   3  NH Si(CH3)3
H 250
44   4  O  O pentafluoroethyl
H 70   100
100
100
45   4  O  O trifluoromethyl
H 44-46
100
97.5
46   4  O  O 2,2,2-trifluoroethyl
H 80-83
100
100
100
47   4  O  O 2,2,2-trifluoroethyl
F 73   100
100
48   4  O  O 1,1,2,2-tetrafluoroethyl
H 38-40
100
100
49   4  O  O difluoromethyl
H 67   100
100
50   4  O  O 2,2,3,3-tetrafluoro-
H 85
propyl
51   4  O  O 2,2,2-trifluoro-1-
H oil
methylethyl
52   4  O  O n-propyl     H 67-69
99
100
90
53   4  O  O ethyl        H 80-81
100
100
54   4  O  O i-propyl     H 61-66
100
100
55   4  O  O t-butyl      H 62-63
100
100
56   4  O  O n-butyl      H 56-58
0
0
57   4  O  O 1-ethyl-1-methylpropyl
H oil  100
97.5
58   4  O  O pentyl       H oil  100
59   4  O  O 4-(t-butyl)phenyl
H oil  0
60   4  O  O 4-(trifluoromethyl)-
H 53-55
100
phenyl              90
100
100
61   4  O  O phenyl       H oil  100
62   4  O  O 2-fluorophenyl
H oil  95
63   4  O  O 2,4-difluorophenyl
H 86   100
100
64   4  O  O 4-chlorophenyl
H 74   100
65   4  O  O 2,4-dichlorophenyl
H 94
66   4  O  O 4-cyanophenyl
H 123-125
67   4  O  --O--CF2 --O--
68   4  O  S 3-(trifluoromethyl)-
H oil
69   4  NH O 1,1,2,2-tetrafluoroethyl
H 137- 139
100
100
87.5
100
70   4  NH O trifluoromethyl
H 115-117
100
100
71   4  NH O 2,2,2-trifluoroethyl
H 156  100
100
72   4  NH O 2,2,3,3-tetrafluoro-
H 138
propyl
73   4  NH O 2,2,2-trifluoro-1-
H 162-164
methylethyl
74   4  NH O 2,2,2-trifluoroethyl
Cl
75   4  NH O 2,2,2-trifluoroethyl
F 136  100
100
76   4  NH O ethyl        H 158-160
0
77   4  NH O i-propyl     H 185-187
0
78   4  NH O 2-fluorophenyl
H 146  100
100
79   4  NH O phenyl       H 126-128
50
80   4  NH O 2,4-difluorophenyl
H 139  100
100
81   4  NH O 4-(trifluoromethyl)-
H 137-139
phenyl
82   4  NH Si(CH3)3
H
83   5  O  O difluoromethyl
H 86   100
100
100
84   5  O  O 2,2,2-trifluoroethyl
H 82-84
100
100
100
100
85   5  O  O trifluoromethyl
H 49-51
100
100
100
86   5  O  O 1,1,2,2-tetrafluoroethyl
H 87-89
100
100
100
87   5  O  O 2,2,3,3-tetrafluoro-
H 71
propyl
88   5  O  O i-propyl     H >40  100
100
89   5  O  O t-butyl      H 104-106
100
99.5
90   5  O  O ethyl        H 75-76
100
40
91   5  O  O pentyl       H 60-62
100
100
92   5  O  O 3-(trifluoromethyl)-
H oil  100
phenyl              100
93   5  O  O phenyl       H 100-102
100
94   5  O  O 4-(trifluoromethyl)-
H 76- 79
100
phenyl              100
100
95   5  O  O 2,4-difluorophenyl
H 75-77
96   5  O  O 4-chlorophenyl
H 52
97   5  O  S 3-(trifluoromethyl)-
H 102
phenyl
98   5  NH O 2,2,2-trifluoroethyl
H 177.2
100
100
55
99   5  NH O 2,2,2-trifluoroethyl
F 174-178
100
100  5  NH O 2,2,3,3-tetrafluoro-
H 121
propyl
101  5  NH O 2,2,2-trifluoro-1-
H 145
methylethyl
102  5  NH O i-propyl     H 147-149
100
95
103  5  NH O 3-(trifluoromethyl)-
H 134-136
0
phenyl
104  5  NH O phenyl       H 134-136
100
80
80
80
105  5  NH O 2,4-difluorophenyl
H 158
106  5  CH2
O ethyl        H oil  100
100
100
107  6  O  O 2,2,2-trifluoroethyl
H 101  0
108  6  O  O 4-(trifluoromethyl)-
H 116  0
phenyl
109  6  NH O 2,2,2-trifluoroethyl
H 150  0
110  7  O  O 4-(trifluoromethyl)-
H 80-82
100
phenyl
111  7  NH O 2,2,2-trifluoroethyl
H 151  100
112  7  O  O 2,2,2-trifluoroethyl
H 85   100
113  7  NH O 4-(trifluoromethyl)-
H 218  100
phenyl
114  8  NH O 2,2,2-trifluoroethyl
H 187  100
115  8  O  O 2,2,2-trifluoroethyl
H 95   0
116  9  O  O 1,1,2,2-tetrafluoroethyl
H 60-62
100
100
117  9  O  O 2,2,2-trifluoroethyl
H 109
118  9  O  O 4-(trifluoromethyl)-
H 95-97
phenyl
119  9  NH O 2,2,2-trifluoroethyl
H 217
120  9  NH O 2,2,3,3-tetrafluoro-
H
propyl
121  10 O  O pentafluoroethyl
H 94-95
0
122  10 O  O ethyl        H 87-88
0
123  10 O  O 4-(trifluoromethyl)-
H 110-112
0
phenyl
124  10 O  O phenyl       H 110-112
60
60
125  10 NH O trifluoromethyl
H 166-169
100
80
126  10 NH O ethyl        H 174-176
0
127  11 O  O pentafluoroethyl
H 79-80
100
100
128  11 O  O 2,2,2-trifluoroethyl
H 73- 74
100
129  11 O  O difluoromethyl
H
130  11 O  O n-butyl      H
131  11 O  O 4-(trifluoromethyl)-
H 106-108
100
phenyl              100
100
100
132  11 O  O 3-(trifluoromethyl)-
H oil  100
phenyl              100
133  11 O  O phenyl       H 60   100
100
134  11 O  O 4-chlorophenyl
H 148-150
135  11 NH O trifluoromethyl
H 243-249
0
136  11 NH O ethyl        H 220-222
0
0
137  12 NH O phenyl       H
138  12 NH O 2,2,2-trifluoroethyl
H 84-85
139  13 NH O trifluoromethyl
H 163-164
100
100
140  13 NH O 2,2,2-trifluoroethyl
H 139-140
100
141  13 NH O phenyl       H 157-158
0
142  14 O  O t-butyl      H 75   99
97.5
90
143  14 O  O n-butyl      H 60-61
100
144  14 NH O ethyl        H 164  0
145  15 NH Si(CH3)3
H 133-135
146  15 NH O 1,1,2,2-tetrafluoroethyl
H 153-155
100
45
147  15 NH O 2,2,2-trifluoroethyl
H 149-150
100
97.5
148  15 O  O 1,1,2,2-tetrafluoroethyl
H 41-43
100
100
149  15 O  O 2,2,2-trifluorethyl
H 74-76
100
100
150  15 O  O 3-(trifluoromethyl)-
H 50-60
0
phenyl
151  16 NH O 1,1,2,2-tetrafluoroethyl
H 145-147
100
100
25
100
152  16 NH O 2,2,2-trifluoroethyl
H 150-151
153  16 NH O ethyl        H 155-160
0
154  17 O  O pentafluoroethyl
H 72-74
100
35
155  17 NH O 2,2,2-trifluoroethyl
H 165-166
0
__________________________________________________________________________

The following Table II identifies specific compounds of formula (1) wherein Ar is a group of formula (19) and gives results of testing them in the above described peanut root knot nematode assay.

TABLE II
______________________________________
Nematode
Results
Example                      MP       at 12 ppm
No.     Het     X       Z    °C.
% control
______________________________________
156     2       O       Cl   106-107  0
157     2       NH      F    121-122
158     2       NH      Cl   162-163
159     3       O       Cl   139-140  0
160     3       O       F    126-127
161     3       O       Br   130      100
70
162     3       NH      Br   198-199
163     3       NH      Cl   176-177  0
164     3       NH      I    221-223  0
165     3       CH2
Cl   97       0
100
166     4       O       Cl   57-58    100
167     4       O       Br   64-65    100
168     4       O       F    93-94
169     4       NH      Cl            60
170     4       NH      Br   190-192  100
171     4       NH      F    171-173
172     5       O       Cl   85-87    100
173     5       NH      Cl   197-200  100
174     9       O       Cl   88-90    80
75
175     10      NH      Cl   178.5-180.5
176     11      O       Cl   126-128
1779    11      NH      Cl   271-275  0
178     12      O       Cl   86       0
179     13      NH      Cl   193-194  100
99.5
180     15      NH      Cl   189-190  0
______________________________________

The compounds of formula (1) are known compounds, or they are made using well known chemical procedures The required starting materials are commercially available, or they are readily synthesized using standard procedures. Compounds of formula (1) wherein Het is of formula (2) or (3) can be synthesized, for example, by the methods disclosed in U.S. Pat. No. 5,114,939, issued May 19, 1992, which is hereby incorporated herein by reference. Compounds wherein Het is of formula (4), (5), (6), (7), (8), or (9) can be synthesized, for example, by the methods disclosed in U.S. patent application Ser. No. 07/324,056, filed Mar. 16, 1989, (pending), corresponding to EPA 326329, which is hereby incorporated herein by reference, Compounds wherein Het is of formula (10), (11), (12), or (13) can be synthesized, for example, by the methods disclosed in U.S. Pat. No. 5,034,393, issued Jul. 23, 1991, which is hereby incorporated herein by reference. Compounds wherein Het is of formula (14) can be synthesized, for example, by the methods disclosed in U.S. patent application Ser. No. 07/502,364 filed Mar. 30, 1990, now U.S. Pat. No. 5,137,879 which is hereby incorporated herein by reference. Compounds wherein Het is of formula, (16), or (17) can be synthesized, for example, by the methods disclosed in U.S. patent application Ser. No. 07/502,342, filed Mar. 30, 1990, (pending), corresponding to EPA 452002 which is hereby incorporated herein by reference

The method of this invention is practiced in accordance with standard techniques for the application of nematicides. In general, good nematicidal activity can be expected at rates of 1-10 lbs/acre.

The compounds of formula (1) are typically applied in the form of nematicide compositions which comprise a compound of formula (1) and a phytologically-acceptable inert carrier. The compositions are either concentrated formulations which are dispersed in water for application, or are dust or granular formulations which are applied without further treatment. The compositions are prepared according to procedures and formulae which are conventional in the agricultural chemical art.

Granular compositions usually contain from about 0.5% to about 15% by weight of the compound, dispersed in an inert carrier which consists entirely or in large part of clay or a similar inexpensive substance. Such compositions are usually prepared by dissolving the compound in a suitable solvent, and applying it to a granular carrier which has been preformed to the appropriate particle size, in the range of from about 0.5 to 3 mm. Such compositions may also be formulated by making a dough or paste of the carrier and compound, and crushing and drying to obtain the desired granular particle size. In use, granules are incorporated into the soil before planting, or applied in the furrow with the seed at planting, or applied in a band on top of a seed row, or broadcast and then incorporated into the soil, or used as a side dressing to an established crop.

Dusts containing the compounds are prepared simply by intimately mixing the compound in powdered form with a suitable dusty agricultural carrier, such as kaolin clay, ground volcanic rock and the like. Dusts can suitably contain from about 1% to about 10% of the compound

Nematicides are also applied as dispersions. For example they can be applied as aqueous drenches around growing plants or applied incrementally via an irrigation system. The dispersions in which the compounds are applied are most often aqueous suspensions or emulsions prepared from concentrated formulations of the compounds. Such water-soluble, water-suspendable or emulsifiable formulations are either solids usually known as wettable powders, or liquids usually known as emulsifiable concentrates or aqueous suspensions. Wettable powders, which may be compacted to form water dispersible granules, comprise an intimate mixture of the active compound, an inert carrier and surfactants. The concentration of the active compound is usually from about 10% to about 90% by weight. The inert carrier is usually chosen from among the attapulgite clays, the montmorillonite clays, the diatomaceous earths, or the purified silicates Effective surfactants, comprising from about 0.5% to about 10% of the wettable powder, are found among the sulfonated lignins, the condensed naphthalenesulfonates, the naphthalenesulfonates, the alkylbenzenesulfonates, the alkyl sulfates, and non-ionic surfactants such as ethylene oxide adducts of alkyl phenols.

Emulsifiable concentrates of the compounds comprise a convenient concentration of a compound, such as from about 50 to about 500 grams per liter of liquid, equivalent to about 5% to about 50%, dissolved in an inert carrier which is either a water miscible solvent or a mixture of water-immiscible organic solvent and emulsifiers. Useful organic solvents include aromatics, especially the xylenes, and the petroleum fractions, especially the high-boiling naphthalenic and olefinic portions of petroleum such as heavy aromatic naphtha. Other organic solvents may also be used, such as the terpenic solvents including rosin derivatives, aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol. Suitable emulsifiers for emulsifiable concentrates are chosen from conventional nonionic surfactants, such as those discussed above.

Aqueous suspensions comprise suspensions of water-insoluble compounds of this invention, dispersed in an aqueous vehicle at a concentration in the range from about 5% to about 50% by weight Suspensions are prepared by finely grinding the compound, and vigorously mixing it into a vehicle comprised of water and surfactants chosen from the same types discussed above Inert ingredients, such as inorganic salts and synthetic or natural gums, may also be added, to increase the density and viscosity of the aqueous vehicle It is often most effective to grind and mix the compound at the same time by preparing the aqueous mixture, and homogenizing it in an implement such as a sand mill, ball mill, or piston-type homogenizer.

When applied in the form of a dispersion of the active ingredient in a liquid carrier, it is conventional to refer to application rates in terms of the concentration of active ingredient in the carrier The most widely used carrier is water.

It is equally practical, when desirable for any reason, to apply the compound in the form of a solution in an appropriate organic solvent, usually a bland petroleum oil, such as the spray oils, which are widely used in agricultural chemistry.

The following formulations of compounds of the invention are typical of compositions useful in the practice of the present invention.

______________________________________
A. 0.75 Emulsifiable Concentrate
Compound of Formula (1)   9.38%
"TOXIMUL D"               2.50%
(nonionic/anionic surfactant blend)
"TOXIMUL H"               2.50%
(nonionic/anionic surfactant blend)
"EXXON 200"               85.62%
(naphthalenic solvent)
B. 1.5 Emulsifiable Concentrate
Compound of Formula (1)   18.50%
"TOXIMUL D"               2.50%
"TOXIMUL H"               2.50%
"EXXON 200"               76.50%
C. 1.0 Emulsifiable Concentrate
Compound of Formula (1)   12.50%
N-methylpyrrolidone       25.00%
"TOXIMUL D"               2.50%
"TOXIMUL H"               2.50%
"EXXON 200"               57.50%
D. 1.0 Aqueous Suspension
Compound of Formula (1)   12.00%
"PLURONIC P-103"          1.50%
(block copolymer of propylene oxide
and ethylene oxide, surfactant)
"PROXEL GXL"              .05%
(biocide/preservative)
"AF-100"                  .20%
(silicon based antifoam agent)
"REAX 88B"                1.00%
(lignosulfonate dispersing agent)
propylene glycol          10.00%
veegum                    .75%
xanthan                   .25%
water                     74.25%
E. 1.0 Aqueous Suspension
Compound of Formula (1)   12.50%
"MAKON 10" (10 moles ethyleneoxide
1.00%
nonylphenol surfactant)
"ZEOSYL 200" (silica)     1.00%
"AF-100"                  0.20%
"AGRIWET FR"  (surfactant)
3.00%
2% xanthan hydrate        10.00%
water                     72.30%
F. 1.0 Aqueous Suspension
Compound of Formula (1)   12.50%
"MAKON 10"                1.50%
"ZEOSYL 200" (silica)     1.00%
"AF-100"                  0.20%
"POLYFON H"               0.20%
(lignosulfonate dispersing agent)
2% xanthan hydrate        10.00%
water                     74.60%
G. Wettable Powder
Compound of Formula (1)   25.80%
"POLYFON H"               3.50%
"SELLOGEN HR"             5.00%
"STEPANOL ME DRY"         1.00%
gum arabic                0.50%
"HISIL 233"               2.50%
Barden clay               61.70%
H. Granules
Compound of Formula (1)   5.0%
propylene glycol          5.0%
Exxon 200                 5.0%
Florex 30/60 granular clay
85.0%
______________________________________

Claims

1. A method of inhibiting a nematode population which comprises applying to the locus of a nematode, a nematode inactivating amount of a compound of the formula (1):

Het--X--CH₂ --CH₂ --Ar (1)

or an N-oxide or salt thereof, wherein

Het is a group selected from: ##STR3## X is O, or NH; Ar is a substituted phenyl group of formula (18), or (19). ##STR4## wherein Y is O or S;

R¹ is (C₂ -C₅) alkyl, (C₃ -C₇) branched alkyl, halo (C₁ -C₄) alkyl, phenyl, or phenyl substituted with CF₃, CN or halo;

R² is H, F, or Cl, or R² combines with Y--R¹ to form --CH₂ --CH₂ --O-- or --O--CF₂ --O--; and

2. A method of claim 1 wherein the compound of formula (1) being one that is able to provide at least 80% control when tested in the peanut root knot nematode assay at 12 ppm.

3. A method of claim 2 wherein the compound of formula (1) is one that is able to provide at least 80%. control when tested in the peanut root know nematode assay at 6 ppm.

4. A method of claim 1 wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is halo (C₁ -C₄) alkyl.

5. A method of claim 4 wherein R¹ is selected from CF₃, CHF₂, CF₂ CF₃, CH₂ CF₃, CF₂ CHF₂, CH(CH₃)CF₃, CH₂ CF₂ CF₂ H, and CH₂ CF₂ CF₃.

6. A method of claim 1 wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is a (C₃ -C₆) branched alkyl group.

7. A method of claim 1 wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is a phenyl group that is monosubstituted with one halo or CF₃ group.

8. A method of claim 1 wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is (C₂ -C₅) alkyl.

9. A method of claim 1 wherein the compound of formula (1) is one where the Het group is of formula (2), (3), (4), or (5).

10. A method of claim 10 wherein the Ar group is a substituted phenyl group of formula (16) wherein R¹ is halo (C₁ -C₄) alkyl.

11. A method of claim 11 wherein R¹ is fluoro (C₁ -C₄) alkyl.

12. A method of claim 11 wherein R¹ is selected from CF₃, CHF₂, CF₂ CF₃, CH₂ CF₃, CF₂ CHF₂, CH(CH₃)CF₃, CH₂ CF₂ CF₂ H, and CH₂ CF₂ CF₃.

13. A method of claim 10 wherein the Ar group is a substituted phenyl group of formula (16) wherein R¹ is a (C₃ -C₆) branched alkyl group.

14. A method of claim 9 wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is a phenyl group that is monosubstituted with one halo or CF₃ group.

15. A method of claim 9 wherein the Ar group is a substituted phenyl group of formula (18) wherein R¹ is a (C₂ -C₅) alkyl.

16. A method of claim 1 wherein the compound of formula (1) is 8-fluoro-4-[2-[4-(pentafluoroethoxy)phenyl]ethoxy]quinoline.

17. A method of claim 1 wherein the compound of formula (1) is 8-fluoro-4-[2-4-(t-butoxy)phenyl]ethoxy]quinoline.

18. A method of claim 1 wherein the compound of formula (1) is 8-fluoro-4-[2-4-(n-pentoxy)phenyl]ethoxy]quinoline.

19. A method of claim 1 wherein the compound of formula (1) is 8-fluoro-4-[2-[3-fluoro-4-(2,2,2-trifluoroethoxy)-phenyl]ethoxy]quinoline.

20. A method of claim 1 wherein the compound of formula (1) is 8-fluoro-N-[2-[4-(trifluoromethoxy)phenyl]ethyl]quinoline-4-amine.